CN117396018A - Top-emission organic electroluminescent device - Google Patents
Top-emission organic electroluminescent device Download PDFInfo
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- CN117396018A CN117396018A CN202210734050.7A CN202210734050A CN117396018A CN 117396018 A CN117396018 A CN 117396018A CN 202210734050 A CN202210734050 A CN 202210734050A CN 117396018 A CN117396018 A CN 117396018A
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- organic electroluminescent
- anode
- electroluminescent device
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- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
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- 238000011056 performance test Methods 0.000 description 1
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- 230000011664 signaling Effects 0.000 description 1
- DWRSCILTXDLQBG-UHFFFAOYSA-N silolane Chemical compound C1CC[SiH2]C1 DWRSCILTXDLQBG-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- 125000005504 styryl group Chemical group 0.000 description 1
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- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
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- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- DBVXXBTUAZSUAY-UHFFFAOYSA-N tert-butyl(dimethyl)germanium Chemical group C[Ge](C)C(C)(C)C DBVXXBTUAZSUAY-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical group CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- UMRPCNGKANTZSN-UHFFFAOYSA-N tributylgermanium Chemical group CCCC[Ge](CCCC)CCCC UMRPCNGKANTZSN-UHFFFAOYSA-N 0.000 description 1
- ISEIIPDWJVGTQS-UHFFFAOYSA-N tributylsilicon Chemical group CCCC[Si](CCCC)CCCC ISEIIPDWJVGTQS-UHFFFAOYSA-N 0.000 description 1
- YMSWJBZPRYKQHJ-UHFFFAOYSA-N triethylgermanium Chemical group CC[Ge](CC)CC YMSWJBZPRYKQHJ-UHFFFAOYSA-N 0.000 description 1
- QXTIBZLKQPJVII-UHFFFAOYSA-N triethylsilicon Chemical group CC[Si](CC)CC QXTIBZLKQPJVII-UHFFFAOYSA-N 0.000 description 1
- WLKSSWJSFRCZKL-UHFFFAOYSA-N trimethylgermanium Chemical group C[Ge](C)C WLKSSWJSFRCZKL-UHFFFAOYSA-N 0.000 description 1
- SLAJUCLVZORTHN-UHFFFAOYSA-N triphenylgermanium Chemical group C1=CC=CC=C1[Ge](C=1C=CC=CC=1)C1=CC=CC=C1 SLAJUCLVZORTHN-UHFFFAOYSA-N 0.000 description 1
- VCQDQISTTHQOPS-UHFFFAOYSA-N tripropylgermanium Chemical group CCC[Ge](CCC)CCC VCQDQISTTHQOPS-UHFFFAOYSA-N 0.000 description 1
- MMYRBBZVCDXGHG-UHFFFAOYSA-N tripropylsilicon Chemical group CCC[Si](CCC)CCC MMYRBBZVCDXGHG-UHFFFAOYSA-N 0.000 description 1
- TYCHBGWSCCIDHZ-UHFFFAOYSA-N tritert-butylgermanium Chemical group CC(C)(C)[Ge](C(C)(C)C)C(C)(C)C TYCHBGWSCCIDHZ-UHFFFAOYSA-N 0.000 description 1
- STDLEZMOAXZZNH-UHFFFAOYSA-N tritert-butylsilicon Chemical group CC(C)(C)[Si](C(C)(C)C)C(C)(C)C STDLEZMOAXZZNH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
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Abstract
A top-emission organic electroluminescent device is disclosed. The top emission device comprises an anode, a cathode and a luminescent layer between the anode and the cathode, wherein luminescent doping material lambda in the luminescent layer max Not less than 500nm and not more than 700nm, and the device has the maximum external quantum efficiency conversion rate E=EQE A /EQE B When 500nm is less than or equal to lambda max Less than or equal to 600nm, E is more than or equal to 1.625; when 600nm<λ max ≤700nm，E≥1.850；EQE A And EQE B Respectively top-emitting and bottom-emitting devices at J o Maximum external quantum efficiency; bottom emission devices having exciton recombination regions with peak positions in regions of > 0% and ∈65% of the thickness of the light-emitting layer on the side closer to the anode exhibit more excellent device characteristicsPiece performance. A display assembly comprising the top-emitting device and the use of the top-emitting device in an electronic apparatus, an electronic component module, a display device or a lighting device are also disclosed.
Description
Technical Field
The present invention relates to a top-emission organic electroluminescent device. And more particularly, to a top-emission organic electroluminescent device having a high efficiency conversion rate, and a display assembly including the same.
Background
Since C.W.Tang and Van Slyke in 1987 reported that organic electroluminescent devices with high brightness and low voltage are rapidly developed, with the research of red, green and blue trichromatic monochromatic organic electroluminescent devices becoming more mature, especially the improvement of brightness, service life and other performances of blue light devices, the organic electroluminescent devices have been brought into practical application stages, and are widely applied to electronic products used daily by us. In practical commercial use, large-area, active driving technology is currently the mainstream of organic electroluminescent display technology. To realize large-size display, a TFT back plate driving technology is required, and a conventional Bottom Emission (BE) organic electroluminescent device (hereinafter referred to as a Bottom Emission device) is prepared thereon, which causes a problem of low aperture ratio. Therefore, to realize an actively driven large-area, high-luminance organic electroluminescent display screen, a Top Emission (TE) organic electroluminescent device (hereinafter referred to as a Top Emission device) needs to be applied. In the current commercial organic electroluminescent devices, the requirements of the international electrooptical committee on the color coordinates of the display are generally met by preparing top-emitting organic light emitting devices and adjusting the optical microcavities in the devices.
As described above, the currently commercial device is a top-emission device, but since the top-emission device has an optical microcavity effect, intrinsic characteristics of a material (for example, a spectrum of the top-emission device cannot reflect an intrinsic spectrum shape of a light-emitting layer) are covered, and the top-emission device needs to adjust a microcavity by adjusting a film thickness to obtain a comprehensive evaluation of device performance, so that the number of experiments is increased, the preparation cost is high, and the top-emission device is not the most suitable device structure for performing performance evaluation on a new material. Because the bottom emission device can well reflect the intrinsic characteristics of the material, and is simple to prepare and low in cost, when developing a new material, research and development personnel usually use the bottom emission device to perform initial evaluation on the performance of the new material, and then apply the potential material to the top emission device, so that time and cost are saved. Therefore, it is necessary to investigate the relationship of performance between the bottom emission device and the top emission device having the same device structure. This would save a lot of time and cost in material development and screening if the device performance of the bottom emitting device could be correlated to some extent with that of a top emitting device having the same device structure.
In the organic electroluminescent device structure mature in the industry, an anode, a hole transport region, an emitting layer (EML), an electron transport region and a cathode (the cathode may further include an Electron Injection Layer (EIL), constituting a composite cathode), wherein the hole transport region may include a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), and the electron transport region may include a Hole Blocking Layer (HBL) and an Electron Transport Layer (ETL). Wherein HBL and/or EBL may be selectively present due to different device structures. One or more layers of the same functional layer, such as one or more layers of HIL, may also be used depending on the different requirements of the device and the optimization results.
The working principle of the organic electroluminescent device is that electrons and holes are respectively injected into an electron transmission area and a hole transmission area from the cathode and the anode under the drive of a certain voltage through the anode and the cathode of the device and then respectively migrate to a luminescent layer, the electrons and the holes are combined to form excitons in the luminescent layer, and the excitons are combined to emit visible light. Therefore, studying exciton recombination behavior in the light-emitting layer is an important factor in studying device performance.
Disclosure of Invention
In view of the above problems, the present invention aims to provide a high-efficiency top-emission organic electroluminescent device comprising an anode and a composite cathode, and a light-emitting layer disposed therebetween, the light-emitting layer comprising a light-emitting dopant having a maximum emission wavelength λ max And 500nm is less than or equal to lambda max The top-emission organic electroluminescent device has maximum external quantum efficiency conversion rate E, when 500nm is less than or equal to lambda max E is more than or equal to 1.625 when the wavelength is less than or equal to 600 nm; when 600nm<λ max E is more than or equal to 1.850 when the wavelength is less than or equal to 700 nm; the e=eqe A /EQE B Wherein EQ isE A At current density J for top emission device o Maximum external quantum efficiency under EQE B At current density J for bottom emission device o Maximum external quantum efficiency; the bottom emission device has the same device structure as the top emission device, and has an exciton recombination region, the exciton recombination peak position being located in a region of the light emitting layer having a thickness of more than 0% and less than or equal to 65% on a side close to the anode.
According to one embodiment of the present invention, there is disclosed a top-emission organic electroluminescent device comprising:
an anode, a composite cathode, and a light emitting layer disposed between the anode and the composite cathode;
the luminescent layer comprises a luminescent doping material, and the maximum emission wavelength of photoluminescence spectrum of the luminescent doping material is lambda max And 500nm is less than or equal to lambda max ≤700nm；
The top-emitting organic electroluminescent device has a maximum external quantum efficiency conversion E, e=eqe A /EQE B And conform to: when 500nm is less than or equal to lambda max E is more than or equal to 1.625 when the wavelength is less than or equal to 600 nm; when 600nm <λ max E is more than or equal to 1.850 when the wavelength is less than or equal to 700 nm;
the EQE A At a current density J for the top-emitting organic electroluminescent device o Maximum external quantum efficiency;
the EQE B At current density J for bottom-emitting organic electroluminescent devices o Maximum external quantum efficiency;
the bottom emission organic electroluminescent device has the same device structure as the top emission organic electroluminescent device;
the light-emitting layer of the bottom-emission organic electroluminescent device is provided with an exciton recombination region, and the exciton recombination peak position is positioned in a region, which is more than 0% and less than or equal to 65% of the thickness of one side, close to the anode, of the light-emitting layer of the bottom-emission organic electroluminescent device.
According to one embodiment of the present invention, there is disclosed a top-emission organic electroluminescent device comprising: an anode, a cathode, and a light emitting layer disposed between the anode and the cathode;
the light-emitting layer comprises a light-emitting doping material;
the maximum emission wavelength of photoluminescence spectrum of the luminescent doping material is lambda max And 500nm is less than or equal to lambda max ≤700nm；
The light-emitting layer is provided with an exciton recombination region, and the exciton recombination peak position is positioned in a region, which is more than 0% and less than or equal to 65% of the thickness of one side, close to the anode, of the light-emitting layer.
According to one embodiment of the present invention, a display assembly is also disclosed, comprising a top-emitting organic electroluminescent device as described in the previous embodiments.
According to an embodiment of the present invention, there is also disclosed the use of a top-emitting organic electroluminescent device as described in the previous embodiments in an electronic apparatus, an electronic component module, a display device or a lighting device.
By studying the exciton recombination peak position of the bottom emission device with the same device structure as the top emission organic electroluminescent device and the efficiency conversion rate E between the bottom emission device and the top emission device, the top emission organic electroluminescent device can show more excellent device performance compared with other top emission organic electroluminescent devices even if the same organic light emitting doping material is used.
Drawings
Fig. 1 is a schematic cross-sectional view of a top-emission organic electroluminescent device 100.
Fig. 2 is a schematic cross-sectional view of a bottom-emitting organic electroluminescent device 200.
Fig. 3 is a schematic diagram of the position distribution of the detection layer in the EML.
Fig. 4a is a schematic diagram of exciton fraction distribution at different locations in the EML of bottom-emitting devices examples 1-1, 1-2, and 1-5 in the present invention.
FIG. 4b is a graph showing the maximum external quantum efficiency and the maximum external quantum efficiency conversion E of top emission devices of examples 1-1, 1-2, and 1-5 according to the present invention.
FIG. 5a is a schematic representation of the exciton fraction distribution at various locations in the EML for inventive mid-bottom emission devices examples 1-3, 1-4, and 1-6.
FIG. 5b is a graph showing the maximum external quantum efficiency and the maximum external quantum efficiency conversion E for examples 1-3, 1-4, and 1-6 of the mid-sole emission device of the present invention.
FIG. 6a is a schematic representation of the exciton fraction distribution at various locations in the EML for inventive mid-bottom emission devices examples 1-7, 1-8, and 1-9.
FIG. 6b is a graph showing the maximum external quantum efficiency and the maximum external quantum efficiency conversion E for examples 1-7, 1-8, and 1-9 of the mid-sole emission device of the present invention.
Fig. 7 is a schematic cross-sectional view of a top-emission organic electroluminescent device 300.
Fig. 8 is a schematic cross-sectional view of a bottom-emitting organic electroluminescent device 400.
Fig. 9 is a schematic diagram of exciton fraction distribution at different locations in the EML of bottom-emitting device examples 1-10.
Detailed Description
As used herein, "top" means furthest from the substrate and "bottom" means closest to the substrate. In the case where the first layer is described as being "disposed" on "the second layer, the first layer is disposed farther from the substrate. Unless a first layer is "in contact with" a second layer, other layers may be present between the first and second layers. For example, a cathode may be described as "disposed on" an anode even though various organic layers are present between the cathode and the anode.
As used herein, the term "OLED device" includes an anode layer, a cathode layer, and one or more organic layers disposed between the anode layer and the cathode layer. An "OLED device" may be bottom-emitting, i.e. light from the substrate side (i.e. bottom-emitting device), top-emitting, i.e. light from the package layer side (i.e. top-emitting device), or transparent, i.e. light from both the substrate and package sides.
As used herein, the term "encapsulation layer" may be a film package having a thickness of less than 100 microns, which includes disposing one or more films directly onto the device, or may also be a cover glass (cover glass) that is adhered to the substrate.
As used herein, the term "light extraction layer" may refer to a light diffusion film, or other microstructure having a light extraction effect, or a thin film coating having a light outcoupling effect. The light extraction layer may be disposed on the surface of the substrate of the OLED, or may be disposed at other suitable locations, such as between the substrate and the anode, or between the organic layer and the cathode, between the cathode and the encapsulation layer, on the surface of the encapsulation layer, etc.
The schematic cross-sectional views of the organic electroluminescent device according to the embodiments of the present invention are shown schematically, not by way of limitation, and the figures are not necessarily drawn to scale, and some layer structures in the figures may be added or omitted as needed. The substrate may be fabricated on a variety of substrates such as glass, plastic and metal. The nature and function of the layers and exemplary materials are described in more detail in U.S. patent US7,279,704B2, columns 6-10, the entire contents of which are incorporated herein by reference.
Devices manufactured according to embodiments of the present invention may be incorporated into a variety of consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, heads-up displays, displays that are fully or partially transparent, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptops, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and taillights.
Definition of terms for substituents
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-as used herein, includes straight and branched chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.
Cycloalkyl-as used herein, includes cyclic alkyl. Cycloalkyl groups may be cycloalkyl groups having 3 to 20 ring carbon atoms, preferably 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl are preferred. In addition, cycloalkyl groups may be optionally substituted.
Heteroalkyl-as used herein, a heteroalkyl comprises an alkyl chain in which one or more carbons is replaced by a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, t-butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl. In addition, heteroalkyl groups may be optionally substituted.
Alkenyl-as used herein, covers straight chain, branched chain, and cyclic alkylene groups. Alkenyl groups may be alkenyl groups containing 2 to 20 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-methylvinyl, styryl, 2-diphenylvinyl, 1-methallyl, 1-dimethylallyl, 2-methallyl, 1-phenylallyl, 2-phenylallyl, 3-diphenylallyl, 1, 2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, straight chain alkynyl is contemplated. The alkynyl group may be an alkynyl group containing 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl and the like. Among the above, preferred are ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl and phenylethynyl. In addition, alkynyl groups may be optionally substituted.
Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. Examples of the aryl group include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Example package of non-condensed aryl groupsIncluding phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methylbiphenyl, 4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl and m-tetrabiphenyl. In addition, aryl groups may be optionally substituted.
Heterocyclyl or heterocycle-as used herein, non-aromatic cyclic groups are contemplated. The non-aromatic heterocyclic group includes a saturated heterocyclic group having 3 to 20 ring atoms and an unsaturated non-aromatic heterocyclic group having 3 to 20 ring atoms, at least one of which is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms including at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, thietaneyl, azepanyl and tetrahydrosilol. In addition, the heterocyclic group may be optionally substituted.
Heteroaryl-as used herein, non-fused and fused heteroaromatic groups that may contain 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms, and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, more preferably a heteroaryl group having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furodipyridine, benzothiophene, thienodipyridine, benzoselenophene, selenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-aza-boron, 1, 3-aza-boron, 1-aza-boron-4-aza, boron-doped compounds, and the like. In addition, heteroaryl groups may be optionally substituted.
Alkoxy-as used herein, is represented by-O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or-O-heterocyclyl. Examples and preferred examples of the alkyl group, cycloalkyl group, heteroalkyl group and heterocyclic group are the same as described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, the alkoxy group may be optionally substituted.
Aryloxy-as used herein, is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenoxy. In addition, the aryloxy group may be optionally substituted.
Aralkyl-as used herein, encompasses aryl-substituted alkyl. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthyl-ethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthyl-ethyl, 2- β -naphthyl-ethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, cyano, o-cyanobenzyl, o-chlorobenzyl, 1-chlorophenyl and 1-isopropyl. Among the above, preferred are benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl. In addition, aralkyl groups may be optionally substituted.
Alkyl-as used herein, alkyl-substituted silicon groups are contemplated. The silyl group may be a silyl group having 3 to 20 carbon atoms, preferably a silyl group having 3 to 10 carbon atoms. Examples of the alkyl silicon group include trimethyl silicon group, triethyl silicon group, methyldiethyl silicon group, ethyldimethyl silicon group, tripropyl silicon group, tributyl silicon group, triisopropyl silicon group, methyldiisopropyl silicon group, dimethylisopropyl silicon group, tri-t-butyl silicon group, triisobutyl silicon group, dimethyl-t-butyl silicon group, and methyldi-t-butyl silicon group. In addition, the alkyl silicon group may be optionally substituted.
Arylsilane-as used herein, encompasses at least one aryl-substituted silicon group. The arylsilane group may be an arylsilane group having 6 to 30 carbon atoms, preferably an arylsilane group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenyl silyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, arylsilane groups may be optionally substituted.
Alkyl germanium group-as used herein, alkyl substituted germanium groups are contemplated. The alkylgermanium group may be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkyl germanium groups include trimethyl germanium group, triethyl germanium group, methyl diethyl germanium group, ethyl dimethyl germanium group, tripropyl germanium group, tributyl germanium group, triisopropyl germanium group, methyl diisopropyl germanium group, dimethyl isopropyl germanium group, tri-t-butyl germanium group, triisobutyl germanium group, dimethyl-t-butyl germanium group, methyl-di-t-butyl germanium group. In addition, alkyl germanium groups may be optionally substituted.
Arylgermanium group-as used herein, encompasses at least one aryl or heteroaryl substituted germanium group. The arylgermanium group may be an arylgermanium group having 6-30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of aryl germanium groups include triphenylgermanium group, phenylbiphenyl germanium group, diphenylbiphenyl germanium group, phenyldiethyl germanium group, diphenylethyl germanium group, phenyldimethyl germanium group, diphenylmethyl germanium group, phenyldiisopropylgermanium group, diphenylisopropylgermanium group, diphenylbutylgermanium group, diphenylisobutylglycol group, and diphenyltert-butylgermanium group. In addition, the arylgermanium group may be optionally substituted.
The term "aza" in azadibenzofurans, azadibenzothiophenes and the like means that one or at least two C-H groups in the corresponding aromatic fragment are replaced by nitrogen atoms. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives will be readily apparent to those of ordinary skill in the art, and all such analogs are intended to be included in the terms described herein.
In the present disclosure, when any one of the terms from the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanium, substituted arylgermanium, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino groups, any one or more of which may be substituted with one or at least two groups selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted cycloalkyl having 1 to 20 carbon atoms, unsubstituted heteroaryl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted alkoxy having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted alkenyl having 3 to 30 carbon atoms, aryl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, unsubstituted arylgermanium groups having 6 to 20 carbon atoms, unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphine groups, and combinations thereof.
It will be appreciated that when a fragment of a molecule is described as a substituent or otherwise attached to another moiety, its name may be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered equivalent.
In the compounds mentioned in this disclosure, the hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because of their enhanced efficiency and stability of the device.
In the compounds mentioned in this disclosure, multiple substitution is meant to encompass double substitution up to the maximum available substitution range. When a substituent in a compound mentioned in this disclosure means multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), it means that the substituent may be present at a plurality of available substitution positions on its linking structure, and the substituent present at each of the plurality of available substitution positions may be of the same structure or of different structures.
In the compounds mentioned in this disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless explicitly defined, for example, adjacent substituents can optionally be linked to form a ring. In the compounds mentioned in this disclosure, adjacent substituents can optionally be linked to form a ring, both in the case where adjacent substituents can be linked to form a ring and in the case where adjacent substituents are not linked to form a ring. Where adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic (including spiro, bridged, fused, etc.), as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to further distant carbon atoms. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.
The expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
The expression that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
the expression that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that the two substituents bound to further distant carbon atoms are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
furthermore, the expression that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that, in the case where one of the adjacent two substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
according to one embodiment of the present invention, there is disclosed a top-emission organic electroluminescent device comprising:
an anode, a composite cathode, and a light emitting layer disposed between the anode and the composite cathode;
the luminescent layer comprises a luminescent doping material, and the maximum emission wavelength of photoluminescence spectrum of the luminescent doping material is lambda max And 500nm is less than or equal to lambda max ≤700nm；
The top-emitting organic electroluminescent device has a maximum external quantum efficiency conversion E, e=eqe A /EQE B And conform to: when 500nm is less than or equal to lambda max E is more than or equal to 1.625 when the wavelength is less than or equal to 600 nm; when 600nm<λ max E is more than or equal to 1.850 when the wavelength is less than or equal to 700 nm;
the EQE A At a current density J for the top-emitting organic electroluminescent device o Maximum external quantum efficiency;
the EQE B At current density J for bottom-emitting organic electroluminescent devices o Maximum external quantum efficiency;
the bottom emission organic electroluminescent device has the same device structure as the top emission organic electroluminescent device;
the light-emitting layer of the bottom-emission organic electroluminescent device is provided with an exciton recombination region, and the exciton recombination peak position is positioned in a region, which is more than 0% and less than or equal to 65% of the thickness of one side, close to the anode, of the light-emitting layer of the bottom-emission organic electroluminescent device.
According to one embodiment of the present invention, there is disclosed a top-emission organic electroluminescent device comprising: a first anode, a first composite cathode, and a first hole transport region, a first light emitting layer, a first electron transport region disposed between the first anode and the first composite cathode;
the first hole transport region is between the first anode and the first light emitting layer, and the first electron transport region is between the first light emitting layer and the first composite cathode;
The first luminescent layer comprises a luminescent doping material, and the maximum emission wavelength of photoluminescence spectrum of the luminescent doping material is lambda max And 500nm is less than or equal to lambda max ≤700nm；
The top-emitting organic electroluminescent device has a maximum external quantum efficiency conversion E, e=eqe A /EQE B And:
when 500nm is less than or equal to lambda max E is more than or equal to 1.625 when the wavelength is less than or equal to 600 nm;
when 600nm<λ max E is more than or equal to 1.850 when the wavelength is less than or equal to 700 nm;
the EQE A At current density J for top-emitting organic electroluminescent devices o Maximum external quantum efficiency;
the EQE B At current density J for bottom-emitting organic electroluminescent devices o Maximum external quantum efficiency;
the bottom emission organic electroluminescent device includes: a second anode, a second composite cathode, and a second hole transport region, a first light emitting layer, and a first electron transport region disposed between the second anode and the second composite cathode;
the second hole transport region is between the second anode and the first light emitting layer, and the first electron transport region is between the first light emitting layer and the second composite cathode;
the bottom emission organic electroluminescent device is provided with an exciton recombination region, and the exciton recombination peak position is positioned in a region, which is more than 0% and less than or equal to 65% of the thickness of one side of the first luminescent layer, which is close to the second anode;
The first hole transport region and the second hole transport region comprise the same organic layer or layers, and the types and mass ratios of materials in the organic layers are the same except for the thickness.
According to one embodiment of the present invention, there is disclosed a top-emission organic electroluminescent device comprising: a cathode; an anode; and a light emitting layer disposed between the cathode and the anode;
the light-emitting layer comprises a light-emitting doping material;
the maximum emission wavelength of photoluminescence spectrum of the luminescent doping material is lambda max And 500nm is less than or equal to lambda max ≤700nm；
The light-emitting layer is provided with an exciton recombination region, and the exciton recombination peak position is positioned in a region, which is more than 0% and less than or equal to 65% of the thickness of one side, close to the anode, of the light-emitting layer.
In this embodiment, the exciton recombination zone was obtained by testing a bottom emission device having the same device structure as the top emission device. Specific test methods are explained in this application with respect to the term "exciton recombination peak position".
According to one embodiment of the invention, the first anode/anode has a reflectivity of 85% or more at 550 nm.
According to one embodiment of the invention, the first anode/anode has a reflectivity of 90% or more at 550 nm.
According to one embodiment of the invention, the first anode/anode has a reflectivity of 95% or more at 550 nm.
According to one embodiment of the invention, wherein the first anode/anode is selected from the group consisting of: silver, aluminum, titanium, nickel, platinum, silver, aluminum, titanium, nickel, or a combination of platinum and Indium TiN Oxide (ITO), indium Zinc Oxide (IZO), molybdenum oxide (MoOx), or titanium nitride (TiN), and combinations thereof.
According to an embodiment of the invention, the transmittance of the second anode at 550nm is 80% or more.
According to an embodiment of the invention, the transmittance of the second anode at 550nm is 84% or more.
According to an embodiment of the invention, the transmittance of the second anode at 550nm is 89% or more.
According to an embodiment of the invention, wherein the second anode is selected from the group consisting of: indium Tin Oxide (ITO), indium Zinc Oxide (IZO), molybdenum oxide (MoOx), and combinations thereof.
According to one embodiment of the present invention, wherein, when 500 nm.ltoreq.lambda max When the thickness of the second anode is less than or equal to 600nm, the thickness of the ITO is more than or equal to 700 and less than or equal to
According to one embodiment of the invention, wherein, when 600nm <λ max When the thickness of the second anode is less than or equal to 700nm, the thickness range of the ITO is more than or equal to 1100 and less than or equal to
According to one embodiment of the invention, the exciton recombination peak position is located in a region of the light-emitting layer having a thickness of less than 50% on the side closer to the anode.
According to one embodiment of the invention, the exciton recombination peak position is located in a region of the light-emitting layer having a thickness of less than 40% on the side closer to the anode.
According to one embodiment of the invention, the exciton recombination peak position is located in a region of the light-emitting layer having a thickness of less than 30% on the side closer to the anode.
According to one embodiment of the invention, the exciton recombination peak position is located in a region of the light-emitting layer having a thickness of greater than 2.5% on the side closer to the anode.
According to one embodiment of the invention, the exciton recombination peak position is located in a region of the light-emitting layer having a thickness of greater than 5% on the side closer to the anode.
According to one embodiment of the invention, the exciton recombination peak position is located in a region of the light-emitting layer having a thickness of greater than 7.5% on the side closer to the anode.
According to one embodiment of the invention, the exciton recombination peak position is more than 1nm from the light-emitting layer near the anode side interface.
According to one embodiment of the invention, the exciton recombination peak position is more than 3nm from the light-emitting layer near the anode side interface.
According to one embodiment of the present invention, wherein, when 500 nm.ltoreq.lambda max When the wavelength is less than or equal to 600nm, E is more than or equal to 1.640; preferably, E is not less than 1.660.
According to one embodiment of the invention, wherein, when 600nm<λ max When the wavelength is less than or equal to 700nm, E is more than or equal to 1.900; preferably, E is not less than 2.000.
According to one embodiment of the present invention, wherein, when 500 nm.ltoreq.lambda max When the half-peak width of the photoluminescence spectrum of the luminescent doping material is less than or equal to 600nm, the half-peak width of the photoluminescence spectrum of the luminescent doping material is less than or equal to 53nm; or 45nm or less; or 40nm or less; or 35nm or less.
According to one embodiment of the invention, wherein, when 600nm<λ max When the half-peak width of the photoluminescence spectrum of the luminescent doping material is less than or equal to 700 nm; or 40nm or less; or less than or equal to 35nm; or 30nm or less.
According to one embodiment of the invention, wherein the J o Greater than 5mA/cm 2 And less than or equal to 50mA/cm 2 。
According to one embodiment of the invention, wherein the J o Greater than 5mA/cm 2 And less than or equal to 35mA/cm 2 。
According to one embodiment of the invention, wherein the J o Greater than 5mA/cm 2 And less than or equal to 15mA/cm 2 。
According to one embodiment of the invention, wherein the J o Greater than 1mA/cm 2 And less than or equal to 50mA/cm 2 。
According to one embodiment of the invention, wherein the J o Greater than 3mA/cm 2 And less than or equal to 35mA/cm 2 。
According to one embodiment of the invention, wherein the J o Greater than 5mA/cm 2 And less than or equal to 15mA/cm 2 。
According to one embodiment of the invention, wherein, when 500 nm.ltoreq.lambda max At a wavelength of 600nm or less, in J o Is 10mA/cm 2 Under the condition of EQE B ≥23.0％。
According to one embodiment of the invention, wherein, when 600nm<λ max At a wavelength of less than or equal to 700nm, at J o Is 10mA/cm 2 Under the condition of EQE B ≥24.0％。
According to one embodiment of the invention, wherein, when 500 nm.ltoreq.lambda max At a wavelength of 600nm or less, in J o Is 10mA/cm 2 Under the condition of EQE A ≥37.0％。
According to one embodiment of the invention, wherein, when 600nm<λ max At a wavelength of less than or equal to 700nm, at J o Is 10mA/cm 2 Under the condition of EQE A ≥50％。
According to an embodiment of the invention, the light emitting layer further comprises a first host material and/or a second host material.
According to one embodiment of the invention, the light emitting layer further comprises a first host material and/or a second host material, and the first host material is a p-type host material and the second host material is an n-type material.
According to one embodiment of the present invention, wherein, when 500 nm.ltoreq.lambda max At 600nm or less, the HOMO energy level of the luminescent doped material<-5.100eV。
According to one embodiment of the invention, wherein, when 600nm<λ max At less than or equal to 700nm, the HOMO energy level of the luminescent doping material<-5.110eV。
According to one embodiment of the present invention, the first hole transport region further comprises a first hole injection layer, a first hole transport layer, and/or a first electron blocking layer; the second hole transport region further comprises a first hole injection layer, a second hole transport layer, and/or a first electron blocking layer; wherein the first hole transport layer and the second hole transport layer comprise the same material species and doping ratio, only the thickness is different.
According to one embodiment of the present invention, the first hole transport region further comprises a first hole injection layer, a first hole transport layer, and/or a first electron blocking layer; the second hole transport region further comprises a first hole injection layer, a first hole transport layer, and/or a second electron blocking layer; wherein the first electron blocking layer and the second electron blocking layer comprise the same material type and doping ratio, and only the thickness is different.
According to one embodiment of the invention, the first hole injection layer further comprises a p-type conductivity doping material.
According to one embodiment of the present invention, a display assembly is disclosed that includes the top-emitting organic electroluminescent device of any of the previous embodiments.
According to an embodiment of the present invention, there is disclosed a use of the top-emitting organic electroluminescent device according to any of the preceding embodiments in an electronic device, an electronic component module, a display device or a lighting device.
According to one embodiment of the invention, wherein the luminescent doping material has M (L a ) m (L b ) n (L c ) q Is of the general formula (I);
the metal M is selected from metals with relative atomic mass of more than 40;
L a 、L b 、L c a first ligand, a second ligand and a third ligand which are coordinated with the metal M respectively, and a ligand L a 、L b 、L c May be the same or different;
ligand L a 、L b 、L c Can optionally be linked to form a multidentate ligand;
m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; the sum of M, n, q is equal to the oxidation state of the metal M; when m is greater than or equal to 2, a plurality of L a May be the same or different; when n is 2, two L b May be the same or different; when q is 2, two L c May be the same or different;
ligand L a Has a structure as shown in formula 1 or formula 2:
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Wherein,
cy is selected, identically or differently, for each occurrence, from a substituted or unsubstituted heteroaromatic ring having from 5 to 50 ring atoms;
z is selected from the group consisting of O, S, se, NR ', CR ' R ', siR ' R ' and GeR ' R '; when two R's are present at the same time, the two R's are the same or different;
ring a and ring B are, identically or differently, selected from a substituted or unsubstituted aromatic ring having 6 to 50 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 50 ring atoms, or a combination thereof;
ring a and ring B are each a structure comprising at least two rings fused;
R 1 ，R 2 ，R A and R is B Each occurrence, identically or differently, represents mono-substituted, poly-substituted or unsubstituted;
R’，R 1 ，R 2 ，R A and R is B And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted utensilAlkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 ring atoms, substituted or unsubstituted alkylsilyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted germanium having 0 carbon atoms, carbonyl, cyano, sulfonyl, cyano, carbonyl, sulfonyl, cyano, or any combination thereof;
R 1 And R is 2 At least one of which is selected from halogen, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or cyano;
in formula 1, adjacent substituents R', R 1 And R is 2 Can optionally be linked to form a ring;
in formula 2, adjacent substituents R A And R is B Can optionally be linked to form a ring;
ligand L b And L c The same or different at each occurrence is selected from monoanionic bidentate ligands;
indicating the position coordinated to the metal M.
Herein, "in formula 1, adjacent substituents R', R 1 And R is 2 Can optionally be linked to form a ring ", intended to mean adjacent substitutions thereinGroups, e.g. between two substituents R', two substituents R 1 Between two substituents R 2 Between, substituents R' and R 1 Between, substituents R' and R 2 Between and substituent R 1 And R is 2 In between, any one or more of these substituent groups may be linked to form a ring. Obviously, these substituents may not all be linked to form a ring.
Herein, "in formula 2, adjacent substituents R A And R is B Can optionally be linked to form a ring ", intended to mean groups of substituents adjacent thereto, e.g. two substituents R A Between two substituents R B Between and substituent R A And R is B In between, any one or more of these substituent groups may be linked to form a ring. Obviously, these substituents may not all be linked to form a ring.
According to one embodiment of the invention, wherein the ligand L b And L c Each occurrence is identically or differently selected from any one or both of the following structures:
wherein,
R a ，R b and R is c Each occurrence, identically or differently, represents mono-substituted, poly-substituted, or unsubstituted;
X b and is selected identically or differently on each occurrence from the group consisting of: o, S, se, NR N1 And CR (CR) C1 R C2 ；
X c And X d And is selected identically or differently on each occurrence from the group consisting of: o, S, se and NR N2 ；
R a ，R b ，R c ，R N1 ，R N2 ，R C1 And R is C2 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted, having 1-20 carbon atomsAlkyl of a child, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 ring carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 0 to 20 carbon atoms, carbonyl, sulfonyl, cyano, carbonyl, sulfonyl, cyano, sulfonyl, and combinations thereof;
Adjacent substituents R a ，R b ，R c ，R N1 ，R N2 ，R C1 And R is C2 Can optionally be linked to form a ring.
Herein, "adjacent substituent R a ，R b ，R c ，R N1 ，R C1 And R is C2 Can optionally be linked to form a ring ", intended to mean groups of substituents adjacent thereto, e.g. two substituents R a Between two substituents R b Between two substituents R c Between, substituent R a And R is b Between, substituent R a And R is c Between, substituent R b And R is c Between, substituent R a And R is N1 Between, substituent R b And R is N1 Between, substituent R a And R is C1 Between, substituent R a And R is C2 Between, substituent R b And R is C1 Between, substituent R b And R is C2 Between, and R C1 And R is C2 Between which are locatedAny one or more of these substituent groups may be linked to form a ring. Obviously, these substituents may not all be linked to form a ring.
According to one embodiment of the invention, wherein Cy is any one structure selected from the group consisting of:
wherein,
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution; when there are multiple R in any structure, the R are the same or different;
r is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
Two adjacent substituents R can optionally be joined to form a ring;
wherein, '#' indicates the position of connection with the metal M,the position of the connection to equation 1 is shown.
Herein, "two adjacent substituents R can optionally be linked to form a ring" is intended to mean that any one or more of the substituents of the group consisting of any two adjacent substituents R can be linked to form a ring. Obviously, these substituents may not all be linked to form a ring.
According to one embodiment of the invention, wherein the ligand L a Has a structure represented by any one of the following formulas 1-1, 2-1 to 2-3:
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X 1 and X 2 Is selected identically or differently on each occurrence from C or N, and X 1 And X 2 Not simultaneously C, X 1 And X 2 Not both are N;
y is selected identically or differently for each occurrence from CR y Or N;
Z 1 to Z 4 Is selected from CR, identically or differently at each occurrence z Or N;
x and Z are selected from the group consisting of O, S, se, NR ', CR ' R ', siR ' R ' and GeR ' R '; when two R's are present at the same time, the two R's are the same or different;
R 1 and R is 2 Each occurrence, identically or differently, represents mono-substituted, poly-substituted or unsubstituted;
R’，R 1 ，R 2 ，R z and R is y And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkyl having 3 to 20 ring carbon atoms Cycloalkyl, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, cyano, isocyanate, sulfonyl, mercapto, sulfonyl, and combinations thereof;
R 1 and R is 2 At least one of which is selected from halogen, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, cyano;
In formula 1-1, the adjacent substituents R', R z ，R 1 And R is 2 Can optionally be linked to form a ring;
in formulae 2-1 to 2-3, the adjacent substituents R' and R y Can optionally be linked to form a ring.
Herein, "in formula 1-1, adjacent substituents R', R z ，R 1 And R is 2 Can optionally be linked to form a ring ", is intended to mean groups of substituents adjacent thereto, for example, between two substituents R', two substituents R z Between two substituents R 1 Between two substituents R 2 Between, substituents R' and R 1 Between, substituents R' and R 2 Between and substituent R 1 And R is 2 In between, any one or more of these substituent groups may be linked to form a ring. Obviously, these substituents may also be betweenSo as not to be joined to form a ring.
Herein, "in formulae 2-1 to 2-3, adjacent substituents R' and R y Can optionally be linked to form a ring ", is intended to mean groups of substituents adjacent thereto, for example, between two substituents R', two substituents R y Between, and substituents R' and R y In between, any one or more of these substituent groups may be linked to form a ring. Obviously, these substituents may not all be linked to form a ring.
According to one embodiment of the invention, wherein the luminescent doping material is selected from the group comprising, but not limited to:
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Herein, the bottom emission device has a device structure "same" as the top emission device, or the description referring to the bottom emission device and the top emission device structure "same", or other same meanings, means that each material layer of the bottom emission device and the top emission device between an anode and a composite Cathode (Multi-stack Cathode) is the same, i.e., has the same number of layers, thickness, the same material and doping ratio, except that the thickness of the material layer for adjusting microcavities in the top emission device is different due to microcavity effect. The material layers used to modulate the microcavities are typically Hole Transport Layers (HTLs) and/or Electron Blocking Layers (EBLs). Illustratively, if the top-emitting device is structured as: a first anode/a first hole transport region/a first light emitting layer/a first electron transport region/a first composite cathode; the device structure of the bottom emission device having the "same" device structure as this top emission device is: a second anode/a second hole transport region/a first light emitting layer/a first electron transport region/a second composite cathode; the material types and doping proportions of the layers of the first hole transmission region and the second hole transmission region are identical, except that the thicknesses of the material layers used for adjusting the microcavities are different; the first light emitting layers in the top and bottom emission devices are identical, the first electron transport regions in the top and bottom emission devices are identical, they may each include the same organic layer or layers, and the kinds of materials in each organic layer are the same, and when the organic layers are formed of two or more materials, the doping (mass) ratios of the two or more materials are also the same.
The device structure of the top emission device is the same as that of the bottom emission device, but since the light emitting directions of the bottom emission device and the top emission device are different, the requirements on the electrodes are different. The top-emitted light is emitted from the cathode of the device, thus requiring the cathode to have high light transmittance; and bottom-emitted light is emitted from the anode of the device, thus requiring the anode to have high light transmittance. In bottom emission devices, the anode is typically a transparent or translucent material, including but not limited to ITO, IZO, moOx (molybdenum oxide), etc., with a transparency typically greater than 50%; preferably, the transparency is greater than 70%; the cathode is typically a material with high reflectivity, including but not limited to Al, ag, etc., with a reflectivity greater than 70%; preferably, the reflectivity is greater than 90%. In top-emitting devices, the anode is typically a material or combination of materials with high reflectivity, including but not limited to Ag, ti, cr, pt, ni, tiN, and combinations of the above materials with ITO and/or MoOx (molybdenum oxide), typically with a reflectivity greater than 50%; preferably, the reflectivity is greater than 80%; more preferably, the reflectivity is greater than 90%; the cathode is typically a translucent or transparent conductive material including, but not limited to, mgAg alloy, moOx, yb, ca, ITO, IZO, or combinations thereof, typically having a transparency greater than 30%; preferably, the transparency is greater than 50%.
The term "identical" refers to the same kind of organic material used in the organic layer or region, and if the organic layer is composed of two or more materials, not only the materials are the same, but also the doping ratio is substantially the same (the error of the doping ratio is within +/-5%, i.e., within the region of 95% to 105% of the set doping ratio), while the thickness of the organic layer or region is also substantially the same (the error of the thickness of both is within +/-5%, i.e., within the region of 95% to 105% of the set thickness). The term "the same kind of organic material" as used herein means that the organic materials have the same chemical structural formula.
In this context, the values of HOMO levels (highest occupied orbitals) and LUMO levels (lowest unoccupied orbitals) of all compounds are measured by Cyclic Voltammetry (CV). The test uses an electrochemical workstation model CorrTest CS120, manufactured by marc instruments inc, and uses a three electrode working system: the platinum disk electrode is used as a working electrode, the Ag/AgNO3 electrode is used as a reference electrode, and the platinum wire electrode is used as an auxiliary electrode. The test temperature is 25 ℃, anhydrous DMF is taken as a solvent, tetrabutylammonium hexafluorophosphate of 0.1mol/L is taken as a supporting electrolyte, and the compound to be tested is prepared into 10 -3 And (3) introducing nitrogen into the solution in mol/L for 10min to deoxidize before testing. Instrument parameter setting: the scan rate was 100mV/s, the potential spacing was 0.5mV, and the test window was 1V to-0.5V. In this context, all "HOMO energy levels" and "LUMO energy levels" are negative, with smaller values (i.e., larger absolute values) indicating deeper energy levels; the larger the value (i.e., the smaller the absolute value), the shallower the energy level.
Herein, "composite Cathode" refers to a composite layer composed of a Cathode and an organic layer in contact with the Cathode. In a top-emission device, the "composite cathode" or "first composite cathode" refers to a composite layer composed of the cathode, EIL, and capping layer CPL together. In a bottom emission device, a "composite cathode" or "second composite cathode" refers to a composite layer composed of a cathode and EIL together. For example, in the examples of the present application, the structure of a composite cathode in a top-emitting and bottom-emitting device is shown by way of example and not limitation, respectively, wherein the composite cathode in top-emitting is "pre-vapor deposited" as followsYtterbium (Yb) with a thickness is used as an Electron Injection Layer (EIL), and magnesium (Mg) and silver (Ag) are simultaneously evaporated on the electron injection layer as a Cathode (Cathiode, 10:90, >) Then, a compound CPL is deposited thereon as a capping layer (CPL, ")>) Thereby forming a composite structure ", yb +.>/Mg：Ag(10:90，/>) The transmittance of the double layer structure of (2) is shown in Table 1, wherein +.>The optical refractive index (n value) of the thick CPL material layer at a specific wavelength band is shown in table 2. The composite cathode in the bottom emission device is' vapor deposition first>The thick compound Liq is used as an Electron Injection Layer (EIL), and metal aluminum (Al) is evaporated on the electron injection layer as a Cathode (Cathiode,)>) A composite structure thus formed. The composition of the composite cathode can be adjusted as desired by one skilled in the art, for example, the cathode of the top-emission device is selected from a translucent material or combination such as MgAg alloy, moOx, yb, ca, ITO, IZO, or a combination thereof; the cathode of the bottom emission device is selected from a material or combination with a relatively high reflectivity, such as Ag, ti, cr, pt, ni, tiN, and combinations of the above materials with ITO and/or MoOx; whereas CPL materials are generally selected to have a refractive index greater than 1.8 in the visible region. The EIL layers in the above-described "first composite cathode" and "second composite cathode" may be selected to be suitable materials as needed.
Table 1 YbAg/> Transmittance of film at specific wavelength
| Wavelength (nm) | Transmittance (%) |
| 460 | 58±3 |
| 530 | 53±3 |
| 620 | 43±3 |
TABLE 2CPLOptical refractive index (n value) of film at specific wavelength
| Wavelength (nm) | Refractive index n value |
| 460 | 2.12±0.05 |
| 530 | 1.99±0.05 |
| 620 | 1.88±0.05 |
Yb mentioned aboveAg(10:90，/>) The transmittance test method of the film comprises the following steps: evaporating the +.>Ytterbium (Yb) of a thickness, on which magnesium (Mg) and silver (Ag) are simultaneously evaporated as cathodes (Cathiode, 10:90, ">) Yb/Mg thus formed: the Ag two-layer structure is tested by an ultraviolet spectrophotometer (model is UV 7600) of Shanghai-England optical technology Co., ltd.) to obtain transmittance values under the full wavelength, and after three tests, the average values of the transmittance corresponding to 460nm, 530nm and 620nm are taken.
The optical refractive index (n value) test method of the CPL material mentioned above is as follows: evaporating sample on silicon wafer in evaporating binThe film is tested by adopting an ellipsometer (model is ESNano) of Beijing measuring and rubbing technology Co, and the refractive index n value is obtained, and after three tests, the refractive index average values corresponding to 460nm, 530nm and 620nm are taken.
In this context, the photoluminescence spectrum maximum emission wavelength λ of the organic luminescent doping material max And half-width data test methods such asThe following steps: preparing organic luminescent doping material sample into 1×10 concentration with HPLC-grade toluene -6 The mol/L solution was purged with nitrogen for five minutes by introducing oxygen into the prepared solution, and then excited with light of 400nm wavelength at room temperature (298K) and its luminescence spectrum was measured, and spectral information was directly read from the spectrum, as shown in Table 3; the testing instrument is a fluorescence spectrophotometer with the model of prism F98 manufactured by Shanghai prism technology Co.
TABLE 3 half-width (FWHM) and maximum emission wavelength (lambda) of photoluminescence spectra of luminescent doping materials max ) HOMO energy level data
| Luminescent doping material | λ max (nm) | FWHM(nm) | HOMO(eV) |
| GD-17 | 528 | 31.82 | -5.213 |
| GD-3 | 528 | 34.43 | -5.199 |
| GDA | 525 | 53.37 | -5.051 |
| RD-5 | 619 | 29.79 | -5.145 |
As used herein, "efficiency conversion E" refers to the same current density J o Maximum external quantum efficiency EQE of top emission device A And a bottom emission device having the same device structure as the top emission device, and a maximum external quantum efficiency EQE B Conversion between, i.e. efficiency conversion e=eqe A /EQE B . A luminescent dopant material for adjusting microcavity and obtaining maximum external quantum efficiency EQE by adjusting film thickness of HTL or EBL or combination of the two layers in top-emitting device A The method comprises the steps of carrying out a first treatment on the surface of the The same luminescent doping material is applied to the same bottom-emitting device as the top-emitting device, at a current density J o The second external quantum efficiency measured below is EQE B ，1mA/cm 2 <J o ≤50mA/cm 2 The method comprises the steps of carrying out a first treatment on the surface of the Preferably 3mA/cm 2 <J o ≤35mA/cm 2 The method comprises the steps of carrying out a first treatment on the surface of the More preferably 5mA/cm 2 <J o ≤15mA/cm 2 。
Herein, "exciton recombination peak position" refers to a ratio of a position d of a corresponding detection layer (Probe layer) where the exciton fraction takes a maximum value to the total thickness of the EML, and d represents a distance between an interface (the interface refers to an interface between the contact layer of the EML on the anode side and the EML) and the position of the detection layer. The contact layer of the EML on the anode side includes, but is not limited to, HTL or EBL. "exciton fraction" refers to the ratio of the number of excitons at a position in the light-emitting layer to the total number of excitons in the light-emitting layer. Exciton fraction reflects how much exciton recombination occurs within the diffusion length of the detection layer and can be used to characterize the relative relationship of exciton distribution of the device. Exciton fraction can be calculated from Electroluminescent (EL) spectral data. Taking the example of FIG. 3, where the contact layer of the EML on the anode side is EBL, d represents the probe layer anddistance between EBL/EML interface, total thickness of EML isIf at this time->Obtaining the maximum value of exciton fraction, wherein the corresponding exciton recombination peak position is a region with the thickness of 0/400=0% on the side close to the anode in the light-emitting layer; if at this time +.>When the maximum value of the exciton fraction is obtained, the corresponding exciton recombination peak position is a region with the thickness of 100/400=25% on the side close to the anode in the light-emitting layer; similarly, when- >And->The exciton recombination peak positions corresponding to the regions of the light-emitting layer, which are 50%, 75% and 100% of the thickness of the light-emitting layer near the anode, respectively.
The detection layer mentioned in the exciton recombination peak position test generally comprises a probe material, which is generally selected to be a luminescent dopant material having a similar energy level and electrical properties to the luminescent dopant material in the EML, but which is redshifted from the maximum emission wavelength of the luminescent dopant material in the EML. Preferably, a luminescent doping material with a maximum emission wavelength red shifted by at least 30nm is chosen as probe material. The exciton fraction at the corresponding position of the EML is calculated by comparing the magnitude of the device spectral intensity with or without a probe at each specific position in the light-emitting layer, and the exciton recombination peak position is determined. By way of example and not limitation, top and bottom emission devices are described herein, which use a maximum emission wavelength lambda in bottom emission devices 1-1 through 1-9 max A light-emitting doped material with a wavelength of 500nm or more and 600nm or less, wherein a detection layer comprises a light-emitting layer and a probe material RD01 (lightA spectral peak wavelength of 620 nm) is 1%; for the bottom emission devices 1-10 of the present application, a maximum emission wavelength lambda is used max The detection layer of the luminescent doping material is composed of a luminescent layer and a probe material (RD 02) in a device to be detected, wherein the luminescent doping material is more than 600nm and less than or equal to 700nm, and the doping proportion of RD02 (the photoinduced spectrum peak wavelength is 649 nm) is 1%. Exciton fraction can be calculated from the peak wavelength intensity of the probe material in the electroluminescent spectrum (EL) of the device with the probe layer.
In the case where the device structures of the top and bottom emission devices are identical, the exciton recombination peak position of the bottom emission device is tested, which may characterize the position of the exciton recombination peak of the top emission device corresponding to the identical device structure, or the position of the exciton recombination peak in the top emission device may slightly move in the anode direction with respect to the tested bottom emission device. Microcavity effects exist in the top-emission devices as mentioned previously, so exciton recombination peak locations in devices are typically tested by bottom-emission devices. When the peak position of the exciton recombination zone in the bottom emission device is within a certain range, then the peak position of the exciton recombination zone of the top emission device also fluctuates within a small range corresponding to the peak position of the exciton recombination zone of the bottom emission device. Therefore, researching the peak position of the exciton recombination zone of the bottom emission device is an efficient and reliable means for researching the performance of the top emission device.
The exciton recombination peak position in the light emitting layer of the device can be adjusted in various ways, such as a hole/electron injection layer, a hole/electron transport layer, a hole/electron blocking layer, etc., but the inventors of the present application have studied that the EML layer has a particularly important role in the exciton recombination position in the OLED device. The EML generally comprises a host material and a light-emitting dopant material, wherein the host material is generally classified into a P-type host material, an N-type host material, or a bipolar host material according to its transmission characteristics, and the host material may be one or more according to necessity, for example, two host materials are included in the EML. The difference in transport characteristics and energy levels of the light-emitting dopant material may also affect the transport of carriers in the EML, and thus the recombination sites of excitons. Therefore, we can regulate the exciton recombination peak position in EML by regulating the ratio of various host materials in EML, the doping concentration of the luminescent doping material, etc. For example, when two host materials, i.e., a P-type host material and an N-type host material, are included in the EML, the hole transport capacity in the EML can be improved by increasing the proportion of the P-type host material, so that the exciton recombination region moves to the cathode side; conversely, increasing the proportion of the N-type host material provides electron transport capability in the EML, which causes the exciton recombination zone to move to the anode side. In addition, if a light-emitting doping material with a strong Hole trapping capability is selected, holes transmitted to the EML are rapidly trapped by the light-emitting doping material, and then the exciton recombination zone is close to the anode side; conversely, if the light-emitting dopant material does not have a strong hole-trapping ability, the exciton recombination zone may be away from the anode side.
Although the top-emission device is a device structure in commercial use at present, since the top-emission device has an optical microcavity effect, intrinsic characteristics of materials are masked (for example, a light-emitting spectrum of the top-emission device cannot reflect intrinsic spectral characteristics of a light-emitting layer), and the top-emission device needs to be fully evaluated by adjusting a thickness of a part of an organic layer (for adjusting microcavity), so that a device structure with optimal device performance is finally obtained. Therefore, the performance of the new material is evaluated by using the top emission device, which increases the number of experiments and the test cost, and is not the most suitable material screening device structure. The bottom emission device can well reflect the intrinsic characteristics of materials, and is simple to prepare and low in cost, so that the initial performance test and screening of the new material mostly adopt the structure of the bottom emission device. When developing new materials, research and development personnel generally adopt a bottom emission device structure to perform preliminary screening on the performances of the new materials, and then apply potential materials to top emission devices to perform performance evaluation so as to save time and cost.
Because the organic electroluminescence is current-driven luminescence, the quantum efficiency can effectively reflect the quality of the organic luminescence performance, and is the most important parameter for measuring the performance of the device. EQE refers to the ratio of the number of photons finally emitted by an organic electroluminescent device to the number of injected carriers, reflecting the overall luminous efficiency of the device, and is one of the important parameters for evaluating the performance of the device. Therefore, it is very critical to study the efficiency conversion between top-emitting devices and bottom-emitting devices, which can greatly save time and cost for material development and screening.
The inventor of the application finds through research that when the exciton recombination peak position of a bottom emission device is in a region that the thickness of a light-emitting layer at one side from an anode is more than 0 and less than or equal to 65%, the maximum external quantum efficiency conversion rate from the bottom emission device to a top emission device with the same device structure is higher, and at the moment, the device performance of the top emission device corresponding to the bottom emission device can also reach an excellent level; and a bottom emission device having an exciton recombination peak position in a region of the light emitting layer greater than 65% from the anode side, the bottom emission device having a lower maximum external quantum efficiency conversion to a top emission device having the same device structure, and the top emission device corresponding to the bottom emission device also having poor performance. Meanwhile, even when the EQE of the bottom emission device is equivalent at this time, for example, for a device whose EQE is 23% in the bottom emission device, if the maximum external quantum efficiency conversion rate E is made to be greater than 1.625 by controlling the exciton recombination peak position, it is predicted that the EQE of the top emission having the same device structure will be greater than 23% by 1.625=37%, i.e., the present inventors have found that when the exciton recombination peak position is located in the region where the thickness of the light emitting layer is greater than 0 and less than or equal to 65% from the anode side, the maximum emission wavelength λ max A light-emitting doping material of 500nm or more and 600nm or less, and the maximum external quantum efficiency conversion rate from the bottom emission device to the top emission device with the same device structure can reach 1.625 or more; for lambda max The maximum external quantum efficiency conversion rate from the bottom emission device to the top emission device with the same device structure can reach 1.850 and above. This means that the material system of the bottom emission device can be directly applied to the top emission device structure to obtain ideal device performance, thereby greatly reducing the input resources and time required by researchers to optimize the top emission device, accelerating the development progress, reducing the development cost, and realizing the commercial use of OLED technologyThe development of transformation is significant.
In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, a vapor deposition machine manufactured by Angstrom Engineering, an optical test system manufactured by Frieda, st. John's, an ellipsometer manufactured by Beijing, etc.), in a manner well known to those skilled in the art. Since those skilled in the art are aware of the relevant contents of the device usage and the testing method, and can obtain the intrinsic data of the sample certainly and uninfluenced, the relevant contents are not further described in this patent.
Examples
Hereinafter, the present invention will be described in more detail with reference to the following examples. The compounds used in the following examples are readily available to those skilled in the art, and thus, their synthesis is not described in detail herein. It will be apparent that the following examples are for illustrative purposes only and are not intended to limit the scope of the invention. Based on the following examples, a person skilled in the art is able to obtain other embodiments of the invention by modifying them.
Bottom emission device example:
bottom emission device 1-1: preparation of green phosphorescent bottom-emitting organic electroluminescent device 200 as shown in FIG. 2
Using 0.7mm thick glass substrate with pre-patterned indium tin oxide ITOThe thickness as the second anode 210, after which the substrate is washed with deionized water and a detergent, the ITO surface is treated with oxygen plasma and UV ozone, the substrate is baked in a glove box to remove moisture, and loaded into a holder and transferred into a vacuum chamber; the organic layer specified below was at a vacuum level of about 10 -6 In case of Torr +.>Sequentially evaporating on the anode layer by vacuum thermal evaporation: first, vapor deposition of Compound HI as a hole injection layer (HIL,/and a hole injection layer were formed>) 220, evaporation compound HT is used as hole transport layer (HTL, < > >) 230. Then, vapor deposition compound H1 was used as an electron blocking layer (EBL,/-A)>) 240, on which compound H1, compound H2 and compound GD-17 are simultaneously evaporated as first light-emitting layer (EML, 48:48:4, < >>) 250, vapor deposition compound H3 as hole blocking layer (HBL, < >>) 260, the compounds ET and Liq were co-deposited as electron transport layers (ETL, 40:60,) 270. Then, a second composite Cathode layer (Multi-stack Cathode) 280 is deposited, specifically +.>The thick compound LiQ is used as an Electron Injection Layer (EIL) 280a, and then metal aluminum (Al) is evaporated as a Cathode (Cathode,)> ) 280b. The device is then transferred back to the glove box and encapsulated with a glass cover slip 290 to complete the device.
Bottom emission device 1-2:
the manufacturing method of the bottom emission device 1-2 is the same as that of the bottom emission device 1-1 except that the ratio of the compound H1, the compound H2, and the compound GD-17 in the emission layer EML is 47:47:6.
Bottom emission device 1-3:
the manufacturing method of the bottom emission device 1-3 is the same as that of the bottom emission device 1-1 except that the compound H1, the compound H2, and the compound GD-3 are simultaneously evaporated as light-emitting layers in a ratio of 48:48:4.
Bottom emission device 1-4:
the preparation method of the bottom emission device 1-4 is the same as that of the bottom emission device 1-3 except that the ratio of the compound H1, the compound H2, and the compound GD-3 in the emission layer EML is 47:47:6.
Bottom emission device 1-5:
the manufacturing method of the bottom emission device 1-5 is the same as that of the bottom emission device 1-1 except that the ratio of the compound H1, the compound H2, and the compound GD-17 in the emission layer EML is 63:31:6.
Bottom emission device 1-6:
the preparation method of the bottom emission device 1-6 is the same as that of the bottom emission device 1-3 except that the ratio of the compound H1, the compound H2, and the compound GD-3 in the light emitting layer EML is 63:31:6.
Bottom emission device 1-7:
the manufacturing method of the bottom emission device 1-7 was the same as that of the bottom emission device 1-1 except that the compound H1, the compound H2, and the compound GDA were simultaneously evaporated as light emitting layers in a ratio of 47:47:6.
Bottom emission device 1-8:
the preparation method of the bottom emission devices 1 to 8 was the same as that of the bottom emission devices 1 to 7 except that the ratio of the compound H1, the compound H2, and the compound GDA in the emission layer EML was 63:31:6.
Bottom emission device 1-9:
the preparation method of the bottom emission devices 1 to 9 was the same as that of the bottom emission devices 1 to 7 except that the ratio of the compound H1, the compound H2, and the compound GDA in the emission layer EML was 75:19:6.
The detailed device portion structures and thicknesses of the bottom emission devices 1-1 to 1-9 are shown in table 1. Wherein more than one layer of the material used is doped with different compounds in the weight proportions described.
TABLE 4 partial device structures of bottom emission devices 1-1 through 1-9
The structure of the compounds used in the device is shown below:
table 5 summarizes the device performance of bottom emission devices 1-1 through 1-9. Wherein, the color coordinates CIE and the maximum emission peak wavelength lambda max Half-width FWHM and maximum external quantum efficiency EQE B Is carried out at a current density of 10mA/cm 2 Measuring the lower part; the exciton recombination peak position is the position corresponding to the light-emitting layer when the exciton fraction obtained by testing the above-described bottom emission devices 1-1 to 1-9 is maximum.
TABLE 5 device Performance of bottom emission devices 1-1 through 1-9
As can be seen from the above device structure and device performance, the exciton recombination peak positions, such as bottom emission devices 1-2, 1-4, and 1-7, can be adjusted by adjusting the light emitting materials in the light emitting layer, and their device structures differ only in the light emitting doping materials, and their exciton recombination peak positions in the light emitting layer differ; likewise, the exciton recombination peak position can also be adjusted by adjusting the mass ratio of host material and dopant material in the light-emitting layer (including the mass ratio between the two host materials), for example, the bottom emission devices 1-1 to 1-2 compared to 1-5, and 1-3 to 1-4 compared to 1-6, which differ in that the mass ratio of host material and dopant material is different, and the exciton recombination peak position in the light-emitting layer is also different.
As can be seen from table 5 above, the exciton recombination peak positions in the bottom emission devices 1-1 to 1-4 are within more than 0 and less than or equal to 65% of the light emitting layer on the side near the second anode, respectively within the regions of 25%, 25% and 50% of the light emitting layer near the second anode. And the exciton recombination peak position in the bottom emission devices 1-5 to 1-9 is greater than 0 and less than or equal to 65% of the region outside the light-emitting layer on the side close to the second anode.
Top emission device example: the following are examples of top emission devices having the "same" device structure corresponding to the bottom emission devices one by one, that is, the top emission device 1-1 has the "same" device structure as the bottom emission device 1-1, the top emission device 1-2 has the "same" device structure as the bottom emission device 1-2, and the like.
Top emission device 1-1: a green phosphorescent top-emitting organic electroluminescent device 100 was prepared as shown in fig. 1.
First, a glass substrate of 0.7mm thickness is used, on which indium tin oxide ITO patterned beforehand is present/Ag /ITO/>As the first anode 110, the substrate was baked in a glove box to remove moisture, and loaded onto a holder into a vacuum chamber. The organic layer specified below was at a vacuum level of about 10 -6 In case of Torr +.>Sequentially evaporating on the anode layer by vacuum thermal evaporation: first, vapor deposition of Compound HI as a hole injection layer (HIL,/and a hole injection layer were formed>) 120, vapor deposition compound HT is used as hole transport layer (HTL, < >>) 130, at the same time, the HTL acts as a microcavity conditioning layer, by its thickness being about +.>Vicinity adjustment, the maximum value of the external quantum efficiency EQE is obtained. Then, vapor deposition compound H1 was used as an electron blocking layer (EBL,/-A)>) 140, on which compound H1, compound H2 and compound GD-17 are simultaneously evaporated as a first light-emitting layer (EML, 48:48:4, -/-for example)>) 150, evaporation of Compound H3 as hole blocking layer (HBL, ")>) 160, the compounds ET and Liq were co-deposited as electron transport layers (ETL, 40:60,/for>) 170. Then, a first composite Cathode layer (Multi-stack Cathode) 180 is evaporated, specifically +.>Ytterbium (Yb) with a thickness is used as an Electron Injection Layer (EIL) 180a, and magnesium (Mg) and silver (Ag) are simultaneously evaporated as cathodes (Cathiode, 10:90, ">) 180b followed by evaporation of CPL materialAs a capping layer (CPL,)>) 180c. The device is then transferred back to the glove box and encapsulated with a cover glass 190 to complete the device.
The following top emission devices 1-2 to 1-9 each have HTL as a microcavity conditioning layer through a thickness of about Vicinity adjustment, the maximum value of the external quantum efficiency EQE of the corresponding device is obtained.
Top emission device 1-2
The top emission device 1-2 was fabricated in the same manner as the top emission device 1-1, except that the ratio of the compound H1, the compound H2, and the compound GD-17 in the light emitting layer EML was 47:47:6.
Top emission devices 1-3
The top emission device 1-3 was fabricated in the same manner as the top emission device 1-1, except that compound H1, compound H2, and compound GD-3 were simultaneously evaporated as light-emitting layers in a ratio of 48:48:4.
Top emission devices 1-4
The top emission device 1-4 was fabricated in the same manner as the top emission device 1-3, except that the ratio of compound H1, compound H2, and compound GD-3 in the light emitting layer EML was 47:47:6.
Top emission devices 1-5
The top emission device 1-5 was fabricated in the same manner as the top emission device 1-1 except that the ratio of compound H1, compound H2, and compound GD-17 in the light emitting layer EML was 63:31:6.
Top emission devices 1-6
The top emission device 1-6 was fabricated in the same manner as the top emission device 1-3, except that the ratio of compound H1, compound H2, and compound GD-3 in the light emitting layer EML was 63:31:6.
Top emission devices 1-7
The top emission device 1-7 was fabricated in the same manner as the top emission device 1-1, except that compound H1, compound H2, and compound GDA were simultaneously evaporated as light emitting layers in a ratio of 47:47:6.
Top emission devices 1-8
The top emission devices 1 to 8 were fabricated in the same manner as the top emission devices 1 to 7 except that the ratio of the compound H1, the compound H2, and the compound GDA in the light emitting layer EML was 63:31:6.
Top emission devices 1-9
The top emission devices 1 to 9 were prepared in the same manner as the top emission devices 1 to 7 except that the ratio of the compound H1, the compound H2, and the compound GDA in the light emitting layer EML was 75:19:6.
The detailed device layer portion structures and thicknesses of the top-emission devices 1-1 to 1-9 are shown in table 1. Wherein more than one layer of the material used is doped with different compounds in the weight proportions described.
TABLE 6 partial device structures of top emission devices 1-1 through 1-9
Table 7 summarizes the device performance of top-emission devices 1-1 through 1-9. Wherein, the color coordinates CIEx and CIEy, the maximum emission peak wavelength lambda max, the half-width FWHM and the maximum external quantum efficiency EQE A Is carried out at a current density of 10mA/cm 2 Measuring the lower part; the efficiency conversion E is at a current density of J o ＝10mA/cm 2 Ratio of maximum external quantum efficiency EQE of top-emitting device and bottom-emitting device of "same" corresponding device structure measured below.
TABLE 7 conversion of device Performance and efficiency for Top-emission devices 1-1 through 1-9
The top emission devices 1-1, 1-2, and 1-5 have the same device structures as the above-described bottom emission devices 1-1, 1-2, and 1-5, respectively. The materials used in the bottom emission devices 1-1, 1-2 and 1-5 are all the same, except that the mass ratio of host material to luminescent dopant material in the EML is different, and the EML is H1: H2: GD-17 (48: 4), H1: H2: GD-17 (47: 6) and H1: H2: GD-17 (63: 3), respectively 1:6). As shown in FIG. 4a, which is a schematic diagram showing the exciton fraction distribution at different positions in the EML of the bottom emission devices 1-1, 1-2 and 1-5, it is known from FIG. 4a that the exciton fraction distribution in the bottom emission devices can be adjusted by adjusting the ratio of P-host, N-host and light-emitting doping material GD-17 in the EML, wherein the exciton fraction maximum values, i.e., exciton recombination peak positions, of the bottom emission devices 1-1 and 1-2 are bothThe exciton recombination peak positions of the bottom emission devices 1-5 are +.>The exciton recombination peak positions are controlled to be 25%, 25% and 75% of the total thickness of the light-emitting layer from the anode side thickness, respectively. In addition, EQEs of bottom emission devices 1-1, 1-2, and 1-5 B 26.22%, 25.46%, and 25.07%, respectively, that is, for bottom emission devices 1-1 and 1-2 having an exciton recombination peak position of 25%, the efficiency is better than that of bottom emission device 1-5 having an exciton recombination peak position of 75%. Further, for a maximum external quantum efficiency conversion E of bottom-to-top emission, the efficiency conversions E of top-emission devices 1-1 and 1-2 were 1.667 and 1.674, respectively, each higher than 1.569 of top-emission device 1-5. If the efficiency conversion rate E of the embodiment 1-1 is 1.569 as that of the comparative example, the EQE in the corresponding top emission device should be 26.22% by 1.667=41.14%, and the actual top emission EQE 43.71% is greatly improved by 2.57% compared with 41.14%, and the improvement is 6.24%; examples 1-2 are the same. Thus, for the maximum emission wavelength lambda max When the bottom emission device satisfies that the exciton recombination peak position is in a region of the light-emitting layer, which is close to the anode, and has a thickness of more than 0 and less than or equal to 65%, and the efficiency conversion rate E is more than 1.625, the bottom emission device can obtain more excellent bottom emission device performance, and can also be expected to obtain more excellent top emission device performance.
Similarly, the top emission devices 1-3, 1-4, and 1-6 have the same devices as the bottom emission devices 1-3, 1-4, and 1-6 described above, respectivelyThe materials used in the bottom emission devices 1-3, 1-4, and 1-6 are all the same, except that the mass ratio of host material and luminescent dopant material in the EML is different. FIG. 5a is a schematic diagram showing exciton fraction distribution at different positions in the EML of bottom emission devices 1-3, 1-4, and 1-6, wherein the maximum exciton fraction, i.e., the exciton recombination peak positions, of bottom emission devices 1-3 and 1-4, respectively, areAnd->The exciton fraction maximum of the bottom emission devices 1 to 6 is +.>The exciton recombination peak positions are controlled to be 25%, 50% and 75% of the total thickness in the light-emitting layer from the anode side thickness, respectively. In addition, the EQEs of examples 1-3 were 24.38% higher than the EQEs of 23.07% in comparative examples 1-6, respectively, in bottom emission, i.e., for examples 1-3 where the exciton recombination peak position was 25%, the efficiency was better than comparative examples 1-6 where the exciton recombination peak position was 75% in bottom emission devices. Further, for the maximum external quantum efficiency conversion E of bottom-to-top emission, the efficiency conversion E of top-emission devices 1-3 and 1-4 were 1.734 and 1.691, respectively, each higher than 1.499 of top-emission devices 1-6. If the efficiency conversion E of examples 1-3 is 1.499 as in comparative examples 1-6, then the corresponding top emission device would have an EQE of 24.38% by 1.499= 36.55%, while the actual top emission EQE 42.36% would be significantly improved by 5.81% over 36.55% by 15.9%. Whereas the EQE in examples 1-4 was 23.02%, which is substantially equal to the EQE 23.07% for comparative examples 1-6, the efficiency conversion E in examples 1-4 was 1.691 higher than 1.499 in comparative examples 1-2 for bottom-to-top emission conversion E. If the efficiency conversion E of examples 1-4 is 1.499 as in comparative examples 1-6, then the EQE in its corresponding top emission device should be 23.03% by 1.499 = 34.52% while its actual top emission EQE 38.93% is substantially increased by 4.41% over 34.52%. Thus, for the following Maximum emission wavelength lambda of photoluminescence spectrum max When the bottom emission device satisfies that the exciton recombination peak position is in a region of the light-emitting layer, which is close to the anode, and has a thickness of more than 0 and less than or equal to 65%, and the efficiency conversion rate E is more than 1.625, the bottom emission device can obtain more excellent bottom emission device performance, and can also be expected to obtain more excellent top emission device performance.
However, the top emission devices 1 to 7, 1 to 8, and 1 to 9 have the same device structures as the bottom emission devices 1 to 7, 1 to 8, and 1 to 9 described above, respectively, and in the bottom emission devices 1 to 7, 1 to 8, and 1 to 9, the exciton fraction distribution in the light emitting layer of the bottom emission devices is adjusted while the mass ratio of the host material and the light emitting doping material GDA in the EML is also adjusted to be different, as shown in fig. 6a, and exciton recombination positions of the bottom emission devices 1 to 7, 1 to 8, and 1 to 9 are 0%, and 75%, respectively. Although the efficiency conversion E of bottom emission to top emission of top emission devices 1-7 and 1-8 was 1.621, 1.603, respectively, a slight improvement over 1.560 of top emission devices 1-9 was achieved. However, since the HOMO level of the light-emitting doped material GDA is shallow, only-5.051 eV, a more remarkable hole trapping phenomenon occurs between the hole and the host material in the EML, so that the hole is trapped on the side close to the anode in the EML once entering the EML, resulting in the occurrence of exciton recombination peak position at the EBL/EML interface, at this time, exciton leakage or unobtrusive electron leakage to the EBL may occur, and even the triplet state concentration is too high in a narrower region may cause quenching, resulting in the reduction of device efficiency. The exciton recombination peak position should therefore not be at the interface of the EML and EBL, but should be at least 1nm away from the interface, preferably 3nm away. Meanwhile, the half-width of the PL spectrum of the light-emitting doping material GDA is 53.37nm, which belongs to a wider spectrum, and even if the GDA has good PLQY and other performances, the conversion rate of bottom emission to top emission is lower, and the efficiency of a top emission device is also lower. Thus, when the HOMO level of the luminescent doped material is deeper than-5.100 eV, such as GD-17 and GD-3 being-5.213 eV and-5.199 eV, respectively; meanwhile, when the PL spectrum half-width thereof is 50.00nm or less, preferably 45.00nm or less, more preferably 40nm or less, such as 31.82nm and 34.43nm for GD-17 and GD-3, respectively, the exciton recombination peak position is more than 0 and 65% or less and not at the EML/EBL interface, more excellent device performance can be obtained.
Table 6 summarizes the top emission devices 1-1 through 1-9 at different current densities J o The efficiency conversion E was measured and recorded at 10mA/cm 2 、15mA/cm 2 、35mA/cm 2 、50mA/cm 2 The efficiency conversion E was measured as follows.
TABLE 6 efficiency conversion E for Top-emission devices 1-1 through 1-9 under different Current Density conditions
| Numbering device | 10mA/cm 2 | 15mA/cm 2 | 35mA/cm 2 | 50mA/cm 2 |
| Top emission device 1-1 | 1.667 | 1.672 | 1.680 | 1.684 |
| Top emission device 1-2 | 1.674 | 1.680 | 1.700 | 1.706 |
| Top emission devices 1-3 | 1.734 | 1.733 | 1.724 | 1.724 |
| Top emission devices 1-4 | 1.691 | 1.703 | 1.729 | 1.738 |
| Top emission devices 1-5 | 1.569 | 1.573 | 1.589 | 1.589 |
| Top emission devices 1-6 | 1.499 | 1.500 | 1.504 | 1.504 |
| Top emission devices 1-7 | 1.621 | 1.617 | 1.604 | 1.605 |
| Top emission devices 1-8 | 1.603 | 1.597 | 1.581 | 1.571 |
| Top emission devices 1-9 | 1.560 | 1.565 | 1.581 | 1.586 |
As shown in Table 6, in the top-emission devices 1-1 to 1-9, when 500 nm.ltoreq.lambda. max And when the thickness of the corresponding bottom emission device is less than or equal to 600nm, the efficiency conversion rate E can be more than or equal to 1.625 under different current densities as long as the corresponding bottom emission device meets the requirement that the exciton recombination peak position is in a region, which is more than 0 and less than or equal to 65%, of the light-emitting layer and is close to the second anode side.
Top emission device 1-10: the red phosphorescent top-emitting organic electroluminescent device 300 is shown in fig. 7.
First, a glass substrate of 0.7mm thickness is used, on which indium tin oxide ITO patterned beforehand is present/Ag /ITO/>As the first anode 310, the substrate was baked in a glove box to remove moisture, and loaded onto a holder into a vacuum chamber. The organic layer specified below was at a vacuum level of about 10 -6 In case of Torr +.>Sequentially evaporating on the anode layer by vacuum thermal evaporation: first, compounds HT1 and PD were simultaneously evaporated as hole injection layers (HIL, 97:3,/I)>) 320, vapor deposition compound HT1 is used as hole transportTransfusion layer (HTL,)>) 330, at the same time, the HTL acts as a microcavity conditioning layer, by its thickness being about +.>Vicinity adjustment, the maximum value of the external quantum efficiency EQE is obtained. Then, vapor deposition compound EB was used as electron blocking layer (EBL, ">) 340, on which compound RH and compound RD-5 are simultaneously evaporated as first luminescent layer (EML, 97:3,/respectively>) 350, the compounds ET1 and Liq were co-deposited as electron transport layers (ETL, 140:210,) 360. Thereafter, a top-emitting first composite Cathode layer (Multi-stack Cathode) 370, in particular, vapor depositionYtterbium (Yb) with a thickness is used as an Electron Injection Layer (EIL) 370a, and magnesium (Mg) and silver (Ag) are simultaneously evaporated as cathodes (Cathiode, 14:126, ">) 370b, followed by evaporation of CPL material as capping layer (CPL, ">) 370c. The device is then transferred back to the glove box and packaged with a glass cover slip 380 to complete the device.
Bottom emission device 1-10: a red phosphorescent bottom-emitting organic electroluminescent device 400 having the same device structure as the top-emitting devices 1 to 10 was prepared as shown in fig. 8.
Preparation of devices 1-10 for top emissionThe method was the same except that a glass substrate having a thickness of 0.7mm was used with indium tin oxide ITO patterned in advanceThe substrate is baked in a glove box to remove moisture and loaded into a bracket and transferred into a vacuum chamber after being washed with deionized water and a detergent; except that the evaporation compound HT1 is used as hole transport layer (HTL, < CHEM >>) 430; except for a vapor-deposited bottom-emitting second composite Cathode layer (Multi-stack Cathode) 470, in particular, vapor-deposited +>The thick compound LiQ is used as an Electron Injection Layer (EIL) 470a, and then metal aluminum (Al) is evaporated as a Cathode (Cathode,)>)470b。
Table 7 shows the partial device structures of the top-emission devices 1-10 and the bottom-emission devices 1-10, wherein more than one layer of the material used was doped with different compounds in the weight ratios described.
TABLE 7 device Structure of partial organic layers in Top-and bottom-emission devices 1-10
The compounds newly used in the device are shown below:
tables 8 and 9 summarize the device performance of top-emission devices 1-10 and bottom-emission devices 1-10. Wherein, the color coordinates CIEx and CIEy are the mostLarge emission peak wavelength lambda max The half-width FWHM and the maximum external quantum efficiency EQE are at a current density of 10mA/cm 2 Measuring the lower part; the maximum external quantum efficiency conversion E of bottom emission to top emission, which is, as previously described, at a current density of J o ＝10mA/cm 2 The ratio of the maximum external quantum efficiency EQE of the top emission device 1-10 and the bottom emission device 1-10 measured below; the exciton recombination peak position is the position in the light-emitting layer corresponding to the maximum exciton fraction as measured by bottom emission devices 1-10.
TABLE 8 device Performance, exciton recombination peak position, and efficiency conversion for bottom emission devices 1-10
TABLE 9 device Performance, exciton recombination peak position, and efficiency conversion for Top-emission devices 1-10
The exciton fraction distribution measured by the above-described bottom emission devices 1 to 10 is shown in FIG. 9, in which the exciton fraction of the bottom emission devices 1 to 10 is greater than 0 and less than dIs substantially equal to the interval of (2), and thus can be considered to have an exciton fraction of +.>The maximum value, that is, the exciton recombination peak position is at 12.5% of the total thickness from the anode side in the light-emitting layer. Meanwhile, the efficiency conversion E of the bottom emission device 1-10 to the top emission device 1-10 is 1.910. Red device EQE in bottom emission devices 1-10 B Up to 26.86%, which is an EQE achieved by a very excellent red light emitting material in the industry, by reasonably regulating exciton recombination sites, top emission devices with the same device structure also achieve an EQE of up to 51.3% A . Because ofThis is the maximum emission wavelength lambda for the photoluminescence spectrum max When the bottom emission device satisfies that the exciton recombination peak position is in a region of the light-emitting layer, which is close to the anode, and has a thickness of more than 0 and less than or equal to 65%, and the efficiency conversion rate E is more than 1.850, the bottom emission device can obtain more excellent bottom emission device performance, and can also be expected to obtain more excellent top emission device performance.
In summary, the present invention discloses a high-efficiency top-emission organic electroluminescent device, which is obtained by adjusting the exciton recombination peak position and the efficiency conversion rate E, thereby obtaining a top-emission device with excellent device performance. Compared with other organic electroluminescent devices, the top-emission organic electroluminescent device has more excellent performance, and the same organic luminescent doping material can show more excellent device performance.
It should be understood that the various embodiments described herein are by way of example only and are not intended to limit the scope of the invention. Thus, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific and preferred embodiments described herein. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the invention. It is to be understood that the various theories as to why the present invention works are not intended to be limiting.
Claims (16)
1. A top-emitting organic electroluminescent device comprising:
an anode, a composite cathode, and a light emitting layer disposed between the anode and the composite cathode;
the luminescent layer comprises a luminescent doping material, and the maximum emission wavelength of photoluminescence spectrum of the luminescent doping material is lambda max And 500nm is less than or equal to lambda max ≤700nm；
The top-emitting organic electroluminescent device has a maximum external quantum efficiency conversion E, e=eqe A /EQE B And conform to: when 500nm is less than or equal to lambda max E is more than or equal to 1.625 when the wavelength is less than or equal to 600 nm; when 600nm<λ max E is more than or equal to 1.850 when the wavelength is less than or equal to 700 nm;
the EQE A At a current density J for the top-emitting organic electroluminescent device o Maximum external quantum efficiency;
the EQE B At current density J for bottom-emitting organic electroluminescent devices o Maximum external quantum efficiency;
the bottom emission organic electroluminescent device has the same device structure as the top emission organic electroluminescent device;
the light-emitting layer of the bottom-emission organic electroluminescent device is provided with an exciton recombination region, and the exciton recombination peak position is positioned in a region, which is more than 0% and less than or equal to 65% of the thickness of one side, close to the anode, of the light-emitting layer of the bottom-emission organic electroluminescent device.
2. A top-emitting organic electroluminescent device comprising:
An anode;
a cathode;
and a light emitting layer disposed between the anode and the cathode;
the light-emitting layer comprises a light-emitting doping material;
the maximum emission wavelength of photoluminescence spectrum of the luminescent doping material is lambda max And 500nm is less than or equal to lambda max ≤700nm；
The light-emitting layer is provided with an exciton recombination region, and the exciton recombination peak position is positioned in a region, which is more than 0% and less than or equal to 65% of the thickness of one side, close to the anode, of the light-emitting layer.
3. The top-emission organic electroluminescent device according to claim 1 or 2, wherein the anode has a reflectance at 550nm of 85% or more;
preferably, the anode has a reflectance at 550nm of 90% or more;
more preferably, the anode has a reflectance of 95% or more at 550 nm.
4. The top-emission organic electroluminescent device as claimed in claim 1 or 2, wherein the exciton recombination peak position is located in a region of the light-emitting layer having a thickness of less than 50% on a side close to the anode;
preferably, the exciton recombination peak position is located in a region of the light-emitting layer, which is less than 40% thick on the side close to the anode;
more preferably, the exciton recombination peak position is located in a region of the light-emitting layer having a thickness of less than 30% on the side closer to the anode.
5. The top-emission organic electroluminescent device of claim 1 or 2, wherein the exciton recombination peak position is more than 1nm away from the light-emitting layer near the anode side interface;
Preferably, the exciton recombination peak position is more than 3nm away from the light-emitting layer near the anode side interface.
6. The top-emitting organic electroluminescent device as claimed in claim 1, when 500 nm.ltoreq.λ max When the wavelength is less than or equal to 600nm, E is more than or equal to 1.640; preferably, E is not less than 1.660.
7. The top-emitting organic electroluminescent device of claim 1, when 600nm<λ max When the wavelength is less than or equal to 700nm, E is more than or equal to 1.900; preferably, E is not less than 2.000.
8. The top-emission organic electroluminescent device as claimed in claim 1 or 2, wherein when 500nm +.lambda. max When the half-peak width of the photoluminescence spectrum of the luminescent doping material is less than or equal to 600nm, the half-peak width of the photoluminescence spectrum of the luminescent doping material is less than or equal to 53nm;
preferably, the half-peak width of the photoluminescence spectrum of the luminescent doping material is less than or equal to 45nm;
more preferably, the half-width of the photoluminescence spectrum of the luminescent doping material is 40nm or less;
most preferably, the half-width of the photoluminescence spectrum of the luminescent doping material is less than or equal to 35nm.
9. The top-emitting organic electroluminescent device as claimed in claim 1 or 2, when 600nm<λ max When the half-peak width of the photoluminescence spectrum of the luminescent doping material is less than or equal to 700 nm;
preferably, the half-peak width of the photoluminescence spectrum of the luminescent doping material is less than or equal to 40nm;
More preferably, the half-width of the photoluminescence spectrum of the luminescent doping material is less than or equal to 35nm;
most preferably, the half-width of the photoluminescence spectrum of the luminescent doping material is less than or equal to 30nm.
10. The organic electroluminescent device of claim 1, wherein the J o Greater than 5mA/cm 2 And less than or equal to 50mA/cm 2 ；
Preferably, said J o Greater than 5mA/cm 2 And less than or equal to 35mA/cm 2 ；
More preferably, the J o Greater than 5mA/cm 2 And less than or equal to 15mA/cm 2 。
11. The top-emitting organic electroluminescent device as claimed in claim 1, when 500 nm.ltoreq.λ max At a wavelength of 600nm or less, in J o Is 10mA/cm 2 Under the condition of EQE B More than or equal to 23.0 percent; when 600nm<λ max At a wavelength of less than or equal to 700nm, at J o Is 10mA/cm 2 Under the condition of EQE B ≥24.0％。
12. The top-emitting organic electroluminescent device of claim 1, wherein when λmax is 500 nm.ltoreq.600 nm, at J o Is 10mA/cm 2 Under the condition of EQE A More than or equal to 37.0 percent; when 600nm<λ max At a wavelength of less than or equal to 700nm, at J o Is 10mA/cm 2 Under the condition of EQE A ≥45.0％。
13. The top-emitting organic electroluminescent device of claim 1 or 2, the light-emitting layer of the top-emitting organic electroluminescent device further comprising a first host material and/or a second host material;
preferably, the light emitting layer further comprises a first host material and a second host material, and the first host material is a P-type material and the second host material is an N-type material.
14. The top-emitting organic electroluminescent device as claimed in claim 1 or 2, when 500 nm.ltoreq.λ max At less than or equal to 600nm, the HOMO energy level of the luminescent doping material<5.100eV; when 600nm<λ max At less than or equal to 700nm, the HOMO energy level of the luminescent doping material<-5.110eV。
15. A display assembly comprising the top-emitting organic electroluminescent device as claimed in any one of claims 1 to 14.
16. Use of a top-emitting organic electroluminescent device as claimed in any one of claims 1 to 14 in an electronic apparatus, an electronic component module, a display device or a lighting device.
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